Phenylacetylene → 3-(Phenylethynyl)-1-benzofuran-5-carbaldehyde

HRID 2261095Notes

Reaction equation

HRID 2261095 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1.[Cu]I>[C:13]1([C:19]#[C:20][C:2]2[C:6]3[CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=[CH:10][C:5]=3[O:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 574696633-Bromo-1-benzofuran-5-carbaldehyde

Product 1

HCID 574696653-(Phenylethynyl)-1-benzofuran-5-carbaldehydeYield 56%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

In a dry flask 3-Bromo-1-benzofuran-5-carbaldehyde (1 g, 4.4 mmol) were dissolved in anhydrous THF (50 ml). To this was added under Argon Bis (triphenylphosphine) palladium(II) chloride (160 mg, 0.2 mmol), TEA (2.81 mL, 5 eq.), CuI (40 mg, 0.2 mmol) and Phenylacetylene (897 mg, 8.8 mmol). The reaction was heated at 55° C. for 2 days. The crude was filtered through celite and purified on silicagel using as eluent cyclohexan-ethyl acetate (7-3) affording 680 mg (yield: 56%)

Workup

  1. additionTo this was added under Argon Bis (triphenylphosphine) palladium(II) chloride (160 mg, 0.2 mmol)
  2. filtrationThe crude was filtered through celite
  3. custompurified on silicagel
  4. customaffording 680 mg (yield: 56%)

Sources & evidence

ORD record
ord-5485e938c9a24b97b4fba4b98ca3539d
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

Loading…